When I was a student pilot, I was lucky to have some grizzled mentors. There were a lot of “do this” and “don’t do that” admonitions, a lot of tips regarding shortcuts and rules of thumb, plus some sage advice about decision-making. A lot of that advice could be broken down into the old “It’s better to be on the ground wishing you in the air than to be in the air wishing you were on the ground” genre, but it was often accompanied by a “Let me tell you what I learned the hard way” kind of introduction.
Later, as I gained experience, other pilots began treating me more as a peer than someone who needed additional knowledge. Looking back, it’s obvious the methodology changed: Once I became something of a peer to other pilots, the questions I might be asked about a planned flight became more detailed and focused on the consequences of my decisions and actions.
